How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to howtodoit@slate.com. Nothing’s too small (or big).

Dear How to Do It,

I have a situation I’m very confused about. My husband and I were married for 31 years. We didn’t have sex for the last 15 years. I shopped and overate to compensate. He was sick for the past five years and very, very sick in the last year. He recently passed away. I started having sexual feelings some time last year. In the past year, we had four caregivers for my husband. The last person to care for him was someone I knew for about a year. “Mark” took excellent care of my husband and helped me out by cleaning the house and doing some general chores. We were both present when my husband died at home. My husband and I loved this person and he loved us in return. Mark held me up at the funeral because I felt pretty shaky and we cried in each other’s arms many times. He promised my husband that he would continue to live here and take care of me.

This person is the most caring person I have ever met in my life. I’m 73 but feel about 50, and he is 38. His life has been terrible, and he has several health problems. I planned several conversations to let him know how I felt and never had the nerve to say anything. I tell him he’s awesome, and I wish I were 30 years younger. One day we were giving each other a hug and I blurted out that I would try to seduce him, but I didn’t want to ruin our friendship. Mark replied that he would be open to that. He said that neither his mother nor his ex-wives ever treated him as well as I do.

We have not done the deed. Mark is very shy, and I don’t have much experience with other men. He sent me a picture of his erect penis. I’ve done research on that and realize that may mean that he is really interested because men think their penises are special, great, etc. We’ve had discussions about whether, if we had sex, it would mess either of us up more than we already are. Also, when this phase is over, who is going to feel worse and who would feel jealous when we found someone else? I am in a peculiar position because I’m the one with the money now and he doesn’t have any, but I don’t think less of him because of that. He has a good heart and I love him for that. Could you give me some advice on how to proceed?

—Love After Grief

Dear Love After Grief,

You love him and he’s the most caring person you’ve ever met in your life. Sounds like someone worth having sex with to me. Don’t get bogged down in worry. Age discrepancy only matters when it matters (such as in cases of a party being underage or age-related attraction issues). You’re both OK with the decades between you, and weirder things have happened than a 73-year-old hooking up with a 38-year-old. And yes, the dick pic means he’s interested, and that not only does he think his penis is special, great, etc., but he hopes you do, too. Do you?

It can feel dicey getting into something with someone you have considered a friend, but that circumstance can also make for a beautiful romance. You already have a foundation of respect and care to build on. Who says this phase has to ever end? Who says you have to go on to find someone else? Why can’t this just be the next chapter in your lives—one in which those lives become one shared life? One could abort any blossoming relationship by considering the havoc that a breakup would likely wreak, but if everyone did that, all love would be unrequited, and who wants to live in that world? ’Tis better to have loved and lost, etc.

This is an opportunity that could be very good for both of you. Relax and lean into it, avoiding and ignoring whatever anxiety you may feel to the best of your ability. Don’t let him take you for a ride (beyond the sexual sort)—make sure you keep your finances secure. I wouldn’t recommend sharing your PIN with him, but there’s nothing wrong with sharing your wealth with someone that you care about who has far less. He has a good heart, you say, and I suspect you do as well. Let him have it.

Dear How to Do It,

I am an autistic woman who needs little to no support in daily life, but I’m starting to question my dating choices. A majority of my past relationships ended when other people in my life were kind enough to raise the “get the hell out” alarm and recognized abuse where I couldn’t. I seem to be lacking a BS meter that other people must have; I can also never guess when someone is lying. I am very gullible—I unquestioningly believe it when someone says, “You made me do this to you,” or “A normal woman would do xyz, so you should too.” Now I can recognize these as possible instances of abuse, but only if what the person says matches the exact phrases I’ve memorized as red flags.

I’m very, very tired of having to extract myself from dangerous situations, and I’m rather scared of men now. I’m sorry if this sounds stupid, but if young people are more likely to be selfish and opportunistic, then will the dating pool get better with age? I think most men see my big blue eyes, big boobs, and blond hair before they see my autism (contrary to what is shown on TV, autism does not automatically make people dress sloppily and look visibly disabled), so can I hope to age myself off the radar of would-be abusers when I get to my late 30s and gravity and wrinkles take over? I’ve dated some women and none of them were problematic—should I try to only date women? How can I proceed knowing I have a broken BS meter?

—Not Ready to Give Up

Dear Not Ready to Give Up,

I’m sorry that men have done this to you, and I’m sorry we live in a world where people take advantage of others, especially vulnerable people. Just hearing about this makes me question humanity. I can’t imagine what experiencing it does to your worldview, but I’m glad you haven’t given up. In a brief email to me, Isabelle Hénault, who’s written somebooks about sexuality and the spectrum, told me that the issues you face are very common among adults with autism spectrum disorder. She sad that said vulnerability often comes from a lack of information and skills, and that once people with ASD “learn the steps in relationships, the ‘dating’ game and the notion of consent (giving and checking consent), they will benefit from positive interactions and experiences.” You could check out her books, linked above, for some guidance.

For more on-the-ground information, I spoke with Amy Gravino, a writer, international speaker, and autism consultant whose work often focuses on ASD and sexuality. Gravino, who is on the autism spectrum, told me that when she read your letter, she felt that she was reading about herself. She’s been taken advantage of and made to feel gullible, too. “When you don’t differentiate between positive and negative attention, which a lot of autistic people don’t, it becomes hard to see what abuse can really look like because of how insidious it can be,” said Gravino. So, for example, someone with ASD might easily mistake controlling behavior for loving attention.

Gravino told me she’s employed several strategies to help filter out the bad guys. One is setting her standards high. “If you start out with a standard of ‘I’m different, I’m not allowed to be picky, I have to take all the attention I can get because maybe no one will want to give me attention again,’ it’s hard to go from there,” she explained. She sometimes will have a neurotypical friend help her vet a potential mate by bringing her along when she meets him. She also said that she does have difficulty recognizing abuse unless it’s identical to what she has already experienced, but breaking it down into pieces and really looking for patterns has helped. Sometimes this means realizing that somebody is not a nice person even if he’s been nice to her in the past. “There’s a certain point where the bad someone’s done ends up outweighing the good,” said Gravino.

Her message to you, though, is that you are not “broken.” “Your BS meter is not broken,” she said. “You are a truthful person and that’s not a bad thing. The problem is that other people are liars. That’s not a you problem, that’s a them problem.” I agree. As for your questions about whether dating gets better with time, it’s hard to say. Abusers come in all ages and target all types. I wouldn’t normally suggest to someone who is bi/pansexual to stick to one area of their wide interest, but if you think you might find it satisfying to date only women, there’s no harm in trying that out. Good luck and take care of yourself—I believe in you.

Dear How to Do It,

This last year has been pretty rough. I’m still in my first year of sobriety after hitting it hard throughout my 20s, which would be reason enough to take a break from dating, but then there’s this other thing going on that has been maybe even harder to come to terms with. Over the past year, the head of my penis has gotten a patch of red, inflamed skin that has been slowly spreading. I went and got comprehensively screened for every STD under the sun and all tests came back negative. After much mucking about and worrying, as I have no insurance to get treatment, I finally was able to visit a dermatologist. The diagnosis came back as lichen simplex chronicus, and is unfortunately very treatment-resistant on the genitals though it is innocuous and not contagious. I have applied high-powered topical steroids to the area with no sign of remission. I have no idea if this will spontaneously resolve within a year or so or if it will continue to be there for the rest of my life. Both are a possibility.

On a good day my junk isn’t looking so great. It could be workable and I would say it’s appearance is a low-medium gross, but it is still obvious. I used to get compliments on my penis being “beautiful,” and though I was no Casanova, I got my fair share. My confidence is now shattered, and I’ve even considered quitting dating altogether. I doubt I will ever be able to have the fast and loose dating life I once had, and now, even the prospect of a woman showing interest in me makes me nervous.

This comes with unfortunate social issues as well, like having to explain to my friends why I’m not dating, and me having to make up some lie because I can’t say, “My dick looks like roadkill and it makes me incredibly insecure.” I am in therapy and taking medication to try to deal with my issues as best as possible. While I imagine it will still be quite a while before I’m out there dating again, I don’t know how I will ever regain my sexual confidence in the face of potentially squicking out any date I might have where we make it to the bedroom. I don’t know how to get around the issue of disclosure if, say the lights are off. I don’t want to surprise anyone, but I also don’t want to be like, “Hey, look I have a skin condition and a scar on my dick. Here’s the rundown: blah blah blah.” I also used to be an avid lover of receiving head, but now the idea of someone getting up close and personal down there makes me feel disgusting. I’m really at a loss. How do I get my mojo back?

—Ashamed

Dear Ashamed,

You get it back through experience, and you don’t have much of that (at least, not with your dick in its current condition) at the moment. You have no idea how women will actually react to your penis because you haven’t actually allowed yourself to be reacted to. Your anxiety is very understandable, but like all anxiety, it’s based on hypotheses and not solid data. Are you being extra sensitive to the change in your penis’s appearance, which results in a sort of dysmorphia that makes it look worse to you than it would someone else? It’s quite possible. I’ve seen my share of unusual dicks—crooked, spotted, bedazzled in pearly penile papules. Sometimes I’ll even ask when something looks particularly suspect but not quite at chancre levels of inflamed. All it takes is a “It’s a birthmark” to send me back on my way. See enough dicks and you start to realize that like the men they’re attached to, they are almost never objectively perfect.

You’re not going to come across dick pigs like me all the time, but if you connect with someone on a level beyond superficial, she’ll be more likely to sympathize with your condition. That might mean taking it slow and dating a bit, but it could be what you need. And yes, you may need to be like: “Hey, look I have a skin condition and a scar on my dick. Here’s the rundown: blah blah blah.” It’s annoying and unfair and a cross to bear, but it’s better to be honest about these things. It’s the hand you’ve been dealt. Play it or fold, your choice.

Dear How to Do It,

I’m a 27-year-old, asexual, aromantic, cis woman. I’m totally OK with not having partner(s) of any gender ever. But I have a problem—my libido might not be high, but I do have one, and I do occasionally want to get off. But I can’t. I’ve been my version of sexually active for three or four years now, and I haven’t got to O-town even once. I’ve tried everything: hands, toys (high-power, low-power, and no-power), different positions, different places (bath time, shower time, bedtime); porn does nothing for me (though I’ve tried that too: straight, lesbian, and gay). So far the most useful advice the internet has given me is to get to know my body and what feels good, and relax and not focus on the “goal,” but after three years of relaxing, getting to know my body, and not focusing on the endgame, it’s hard not to get frustrated.

I feel like I’ve gotten close sometimes, but either orgasms are just way less fun than everyone’s hyped them up to be or I’m not getting there. The most I’m getting is leg cramps. Now I just sort of have as much fun as possible until the urge passes, but that’s about as sad as it sounds. Do you have any other advice? This isn’t a big enough part of my life to spend doctor-appointment money on, so you are kind of my last option—no pressure!

—Orgasmless

Dear Orgasmless,

The nut of your question, if you will, about difficulty orgasming is one of the most often asked queries of How to Do It. To recap, some studies show about 10 percent of women report never having had an orgasm, and for some, orgasms are mere quivers compared to the earth-shatterers others experience. Many factors contribute; one very well could be innate physiology. I’m not comfortable linking your asexuality/aromanticism to your climaxing difficulties, as I don’t believe data exist to support that. Some asexual people orgasm; some sexual people do not.

I understand that you’re ready to throw in the towel, but if you want to give coming another go, you could read a book that legendary sex authority Annie Sprinkle wrote with Beth Stephens, The Explorer’s Guide to Planet Orgasm. At some 120 pages, it’s more exhaustive than what you’d typically find online. It includes a step-by-step method to achieving and maximizing orgasmic potential:

If this doesn’t all sound familiar to you (if you are, for example, not performing Kegel exercises or undulating), it might be worth a look. Sprinkle writes passionately about expanding the definition of orgasm: She gives tips for achieving energy orgasms and breath orgasms, for example. I think all are worth a try.

I implore you not to give up. Sprinkle writes that as we age, we have the potential to become more orgasmic, specifically noting that, “If you are not yet deep into your thirties, you should understand that you are very likely still just learning.” There’s hope for you yet.

More How to Do It

My boyfriend and I (both in our 20s) love phone sex. Our relationship has always been long-distance, so our “oral skills” are so good that mutual masturbation over a phone call is much more satisfying than masturbating alone. We both view this time as essential for maintaining intimacy in our relationship and managing our sex drives. However, I am staying with his family until January. I had met his family before, but they live 10,000 miles away, so we weren’t close. They also live in a country that has extremely conservative views around ideas of sex, dating, and marriage. While his family likes me as a person and treats me very well, they’ve also told me they do not want to think of me as their son/brother’s girlfriend because they do not approve of his choices. Is there a solution where I can protect and respect them while also keeping the fun in my relationship?